How to Build a Creative Career: The Uncomfortable Truth About Uncertainty
The creative industry has a perception problem.
Too many people think it’s easy. Too many people think that if you’re just getting started, you should make money right away. But it’s not easy. It’s not guaranteed. It requires a certain amount of insanity—or ignorance—to even do it.
Someone recently asked me how to get paid to make things for a living.
My answer? Start making things. And get comfortable with being uncertain.
Van Neistat and Why Most People Quit
One of my favorite artists, Van Neistat, calls this mindset the “tolerance of uncertainty.” I heard him mention it on a podcast. I wished he’d talked more about it—so I reached out to him.
Van told me, “That’s why everyone who quits, quits… because of the uncertainty.”
Success in this field isn’t about talent alone; it’s about enduring the discomfort of not knowing. It’s about staying in the game when the path forward is unclear and the rewards are not immediate.
That’s it. That’s the difference between the people who make a living doing this and the ones who don’t.
The ones who succeed are willing to live in that uncertainty—for a long, intolerable amount of time that feels like it’s destroying your life.
Why I Keep Choosing Uncertainty
Over the years, I’ve built a tolerance for uncertainty that would give most people a panic attack.
Living in uncertainty isn't just part of the job—it's the job. I’m at my best there. When I’ve taken the safe route, working in a cubicle or at an ad agency with a steady paycheck, it drained my soul.
Building a tolerance for uncertainty is a prerequisite for what I do.
There’s a rush when you’re rewarded for seeing what others can’t.
You get more work. But also more pressure.
You get the credit. But also the blame when things go wrong.
And yeah—my mind and body sometimes pay the toll.
But it can also be beautiful.
You see the next move. You see the path forward.
You thrive on potential. You mute the details.
You see the glass as half full.
Five Ways I’ve Built My Tolerance for Creative Uncertainty
Here’s how I’ve managed the intolerable parts and raised my tolerance over time:
Collaboration. Work with like-minded people. There’s social solidarity in that.
Focus on the first step. Don’t worry about step 17 when step one hasn’t even started.
Embrace naivety. Walk into situations believing you’re the one for the job—even if you don’t have all the answers yet.
Avoid perfection paralysis. Striving for perfection leads to failure. Creative projects are inherently imperfect.
Define your own certainty. Everyone’s tolerance is different. Define what certainty looks like for you—your personality, your family, where you live. That’s up to you.
Questions to Ask Yourself
Whether you’re just getting started or looking to make a change, ask:
What are you really good at?
What are you really obsessed with?
What’s the worst-case scenario if you go for it?
What are you willing to put in the reps for, year after year, with no reward?
Do the Work. Then Do It Again.
The biggest reason I can pay my bills doing this is because I’ve done it for a long time.
When you’re starting something new, there are no shortcuts.
You don’t get better pay by researching or waiting for perfect timing.
The only way to do it is to do it—over and over again.
You’re going to eat shit.
Eventually, you might get good.
And if you’re lucky, you get paid.
What’s Your Version of Creative Uncertainty
If you're trying to build your tolerance for uncertainty, I want to hear about it.
What are you working on right now that feels a little bit impossible? Drop me an email or share it with someone who’s also flying blind right now. Uncertainty feels a lot less lonely when we’re in it together.